11β-Hydroxytestosterone

11β-Hydroxytestosterone
Names
	IUPAC name 11β,17β-Dihydroxyandrost-4-en-3-one
	Systematic IUPAC name (1S,3aS,3bS,9aR,9bS,11aS)-1,10-Dihydroxy-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Identifiers
CAS Number	1816-85-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:81481;
ChEMBL	ChEMBL486718;
ChemSpider	102866;
ECHA InfoCard	100.162.057
EC Number	634-040-0;
KEGG	C18075;
PubChem CID	114920;
UNII	BEF7K94MWQ ;
CompTox Dashboard (EPA)	DTXSID70939454 ;
	InChI InChI=1S/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14-,15-,16-,17+,18-,19-/m0/s1;
	SMILES C1C2=CC(CC[C@@]2([C@]3([C@H](C[C@]4([C@]([C@@]3(C1)[H])(CC[C@@H]4O)[H])C)O)[H])C)=O;
Properties
Chemical formula	C19H28O3
Molar mass	304.430 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H351, H360
Precautionary statements	P201, P202, P281, P308+P313, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

11β-Hydroxytestosterone is an endogenous steroid, a metabolite of testosterone.^[1]^[2]^[3]^[4] Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.^[4]

References

^ Storbeck KH, Mostaghel EA (2019). "Canonical and Noncanonical Androgen Metabolism and Activity". Prostate Cancer. Advances in Experimental Medicine and Biology. Vol. 1210. Springer. pp. 239–277. doi:10.1007/978-3-030-32656-2_11. ISBN 978-3-030-32655-5. PMID 31900912. S2CID 209748543. CYP11B1 and 2 have also been shown to 11β-hydroxylate T, yielding 11β-hydroxytestosterone (11OHT), though the levels produced by the adrenal are low due to the limited availability of adrenal derived T
^ Stárka L, Dušková M, Vítků J (September 2020). "11-Keto-testosterone and other androgens of adrenal origin". Physiological Research. 69 (Suppl 2): S187–S192. doi:10.33549/physiolres.934516. PMC 8603739. PMID 33094617.
^ van Rooyen D, Gent R, Barnard L, Swart AC (2018). "The in vitro metabolism of 11β-hydroxyprogesterone and 11-ketoprogesterone to 11-ketodihydrotestosterone in the backdoor pathway". The Journal of Steroid Biochemistry and Molecular Biology. 178: 203–212. doi:10.1016/j.jsbmb.2017.12.014. PMID 29277707. S2CID 3700135.
^ ^a ^b Masiutin M, Yadav M (2023). "Alternative androgen pathways". WikiJournal of Medicine. 10: X. doi:10.15347/WJM/2023.003. S2CID 257943362.

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[pmid31900912-1] Storbeck KH, Mostaghel EA (2019). "Canonical and Noncanonical Androgen Metabolism and Activity". Prostate Cancer. Advances in Experimental Medicine and Biology. Vol. 1210. Springer. pp. 239–277. doi:10.1007/978-3-030-32656-2_11. ISBN 978-3-030-32655-5. PMID 31900912. S2CID 209748543. CYP11B1 and 2 have also been shown to 11β-hydroxylate T, yielding 11β-hydroxytestosterone (11OHT), though the levels produced by the adrenal are low due to the limited availability of adrenal derived T

[pmid33094617-2] Stárka L, Dušková M, Vítků J (September 2020). "11-Keto-testosterone and other androgens of adrenal origin". Physiological Research. 69 (Suppl 2): S187–S192. doi:10.33549/physiolres.934516. PMC 8603739. PMID 33094617.

[pmid29277707-3] van Rooyen D, Gent R, Barnard L, Swart AC (2018). "The in vitro metabolism of 11β-hydroxyprogesterone and 11-ketoprogesterone to 11-ketodihydrotestosterone in the backdoor pathway". The Journal of Steroid Biochemistry and Molecular Biology. 178: 203–212. doi:10.1016/j.jsbmb.2017.12.014. PMID 29277707. S2CID 3700135.

[wj-4] Masiutin M, Yadav M (2023). "Alternative androgen pathways". WikiJournal of Medicine. 10: X. doi:10.15347/WJM/2023.003. S2CID 257943362.

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[2]

[3]

[4]

See also

References